Pyridine → HCID 15009140, compound

HRID 1090063Notes

Reaction equation

HRID 1090063 reaction equation
[I:1][CH2:2][CH2:3][OH:4].Cl[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:7].N1C=CC=CC=1.C(OCC)C>C1C=CC=CC=1>[C:6](=[O:7])([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[O:4][CH2:3][CH2:2][I:1]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 12225IodoethanolHCID 81956Carbonochloridic acid, octyl ester

Product 1

HCID 15009140HCID 15009140, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a well-stirred solution consisting of 17.89 g. (0.104 mole) of 2-iodoethanol dissolved in 25 ml. of benzene precooled to 0° C. with the aid of an ice/water bath, there is added in a dropwise manner a solution consisting of 20 g. (0.104 mole) n-octyl chloroformate dissolved in 25 ml of benzene. Upon completion of this step, the reaction mixture is treated with 8.3 ml (0.104 ml.) of pyridine which is also added in a dropwise manner. The resulting suspension is then stirred for 30 minutes at 0° C. and thereafter for a period of five hours at room temperature while under a nitrogen atmosphere. At the end of this time, 100 ml. of diethyl ether is added to the mixture and the precipitated pyridine hydriodide is then removed by filtration. The organic filtrate is thereafter washed twice with 3N hydrochloric acid and once with brine, followed by drying over anhydrous magnesium sulfate. After removal of the drying agent by means of filtration and the solvent by means of evaporation under reduced pressure, there is obtained 2-iodoethyl n-octyl carbonate as the residual material.

Workup

  1. additionthere is added in a dropwise manner a solution
  2. additionis also added in a dropwise manner
  3. waitfor a period of five hours at room temperature while under a nitrogen atmosphere
  4. customthe precipitated pyridine hydriodide is then removed by filtration
  5. washThe organic filtrate is thereafter washed twice with 3N hydrochloric acid and once with brine
  6. dry with materialby drying over anhydrous magnesium sulfate
  7. customAfter removal of the drying agent
  8. filtrationby means of filtration
  9. customthe solvent by means of evaporation under reduced pressure

Sources & evidence

ORD record
ord-61c769ff5aea4ffbaa1de1eb3b14c22a
Source dataset
uspto-grants-1992_01
Patent number
US05081118

Reaction notes

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